


Halloween, Angels, and Midnight

by Honey_Honey



Category: Supernatural
Genre: Angel Castiel (Supernatural), Bisexual Dean Winchester, Castiel/Dean Winchester First Kiss, Dean Winchester Can't Say "I Love You", GOD FORGIVE ME BUT, Gay Panic, I know, IMPLIED PRAYER SEX, JUST IMPLIED!!!!!, M/M, Praying Dean Winchester, Praying to Castiel (Supernatural), Slow Build Castiel/Dean Winchester, Slow Burn, Telepath Castiel (Supernatural), There's A Tag For That, This is so sad!, Top Castiel/Bottom Dean Winchester, again most likely just IMPLIED, also cas initiates the kiss, also cas tops, also we're in love, anyway, because I said so, cas is so cute lemme go cry, dean thinks castiel is so hot, halloween AU??, i made up this little AU, idk what to call it, im sorry, it's the best jdskajkfds, lol yeahhhh B), more like slow burn ISH, sam is a little shit of a brother, sam is actually like 7 years younger, sorry - Freeform, we only see each other once a year, we'll go with that for now, why? that's simple!, y'all not me having an actual plot for once
Language: English
Status: In-Progress
Published: 2020-10-24
Updated: 2020-11-03
Packaged: 2021-03-09 01:34:29
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 7,198
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27185953
Author URL: https://archiveofourown.org/users/Honey_Honey/pseuds/Honey_Honey
Summary: Every Halloween, from sunset to midnight, creatures from another world walk the earth. They're mostly mirages, unable to touch the inhabitants of our world, unless their connection was forged before time.For Dean Winchester, Halloween is just another day. His dad was obsessed with the holiday, but him? Not so much. He could appreciate it, but the celebrations weren't for him.That is, until he met Castiel, an angel from the other world.Now, October 31st can't come soon enough.ORHot angel who Dean can only see once a year?? Sign him up, tf??
Relationships: Castiel & Dean Winchester, Castiel/Dean Winchester
Comments: 12
Kudos: 21





	1. 2013 - Trench Coat Angel

**Author's Note:**

> Me, starting a new multi-chapter work? Yeah <3 I've fallen down a destiel rabbit hole AGAIN, and I cannot stop writing about them. I hope you guys like this idea :)

**_Thursday, October 31st, 2013_ **

**_10:02pm_ **

23 year old Dean Winchester slid underneath his Impala, tools in hand to fix whatever issue had been plaguing her during their last drive. He was working a late night at the garage, the only employee available halloween night. The extra pay would help, too- it would go toward Sammy’s college tours, which had started last week.

‘Cherry Pie’ by Warrant blasted through Dean’s speakers and he sang along at the top of his lungs, head bobbing as he worked on his car. It was a slow night, which he was fine with. People were out with their families, greeting angels and protecting themselves from demons, children bonding with shapeshifters (who became their ‘imaginary’ friends), and witches saving kittens. Dean knew Sam was smart (they always had symbols and parcels to ward off demons and malevolent creatures on themselves and around the house, keeping themselves safe every halloween), so he left the 16 year old at home alone. Sam was growing up; he trusted him to stay safe.

A rustling sound got his attention. Dean glanced to his right, still under the car, and saw a pair of black dress shoes. “Oh!” He exclaimed, trying to sit up and promptly banging his head on the undercarriage of the Impala. He cursed soundly, sliding out from under the car and standing up. One hand on his forehead, one hand helping him lean on the car, he turned toward the mystery person. “Hi, welcome to Bobby’s Auto Repair- sorry, I was working on this, I can- what can I do for you?”

Dean looked up, his eyes still squinted in pain, but he quickly widened them at what was in front of him.

The man was tall, just a little shorter than Dean. He was wearing a button up shirt with a tie, dress pants, and a tan trench coat. His black hair was a little messy, matching his breathless expression. Dean was mostly focused on his eyes- he was pretty sure that shade of blue was too bright to be an actual eye color- and the seemingly silver haze that trailed the man's movements.

“Oh, I’m- I’m sorry,” the man started, as Dean moved his hand off his forehead, all but staring open mouthed. His voice sent an involuntary blush to Deans face. “I didn’t mean to startle you. I’ll- I’ll go.”

“No!” Dean held his hands out in front of him, eyes wide. The man raised his eyebrows, still looking nervous. “No, um- you’re from… the other world, right?” The other nodded. “Okay, well… I don’t have a lot going on right now. No ones coming to get their cars fixed. Do you wanna hang around? I promise I don’t bite,” he chuckled nervously, scratching the back of his head as he waited for a response.

The man nodded, and Dean felt his heartbeat quicken. “Yeah, okay,” he said, smiling a little as he put his hands in the pockets of his trench coat.

“Okay,” Dean replied, promptly putting his hand out to greet him. He quickly retracted it, turning a bright shade of red as he remembered other world beings couldn’t touch humans. Not unless they had a very strong connection.

Then the man laughed, and Dean felt something like butterflies in his stomach. The sound was almost musical. “My name is Castiel,” said the man, still giving Dean a smile that made him feel like he had to sit down.

“Castiel,” Dean started, unable to keep the smile off his face. “I’m Dean.”

**_11:13pm_ **

Dean's mouth dropped as Castiel finished what he was saying. “You’re kidding, right?” He exclaimed, grinning as the other began laughing. “You’re seriously an angel? _God_ is your _Dad?_ ”

Said angel, who Dean had quickly nicknamed Cas (he liked it. Dean made him smile), nodded. “In a way, it’s not that big of a deal. God is technically your Father, too. Not just for beings in my world.”

Dean barked a laugh, throwing his head back. “Yeah, sure. I don’t think I could view God as my Dad, but you’re sorta right, angel.”

Cas tilted his head, one eyebrow raised. “Are you _calling_ me ‘angel’ now?”

“Oh!” Dean’s whole face went an embarrassingly bright shade of red. “Sorry, I- I wasn’t calling you by your, uh, species? Like, not the same as you calling me ‘human’, but like a-a pet name- this is embarrassing, okay, I can stop if you want-”

Cas laughed again, and it only made Deans face redder. “No, it’s okay,” he responded, his grin dazzling Dean so bad, he felt like his legs were gonna give out from under him. He leaned on the counter behind him. “I kind of like it.”

Dean couldn’t believe his ears. He rolled with it anyway. “Wait, not to go back to the whole God thing, but- can only He hear prayers? Or do angels hear them, too?”

Cas thought for a moment, looking down at the floor between them. Dean watched his hair fall slightly into his face. “Well, it depends. If you pray to God, He’ll hear it, we won’t. But, if you direct it at one of us, then yeah. I would be able to hear it if it was directed at me.”

Dean squinted at him then bowed his head, eyes closed. Cas watched him, half his mind a little confused, the other half unable to look away from Dean slightly parted lips. Then, the angel tilted his head like he was listening to someone's whisper. A smile spread over his lips as Dean opened his eyes and gave him a questioning look.

“I like talking to you, too, Dean,” he said, his smile soft.

Eyes filled with surprise, Dean smiled back.

**_11:57pm_ **

The watch on Dean’s wrist beeped, informing him that it was just about time for him to lock up the garage and go home.

In other words, it was almost midnight. All the beings from the other world would be gone in five minutes.

Dean informed Cas of the time, and he watched the others' expressions drop. His heart twisted (the look on Cas’ face reminded him of a kicked puppy), and he instinctively reached out to put a comforting hand on the angel's shoulder, the way he did whenever Sam had the same look. He remembered too late, when his hand was only inches away, that he wouldn’t be able to touch Cas unless they had some sort of connection, something deeper than whatever kept their worlds apart, which he couldn’t build in only two hours of conversation about prayers and-

Deans hand landed on Cas’ shoulder.

He yanked his hand back in shock, as if he’d been burned. Cas looked up at him, the sadness gone from his face ( _At least he’s not doing the sad puppy eyes anymore,_ Dean thought), his mouth open. “Dean,” he said, before cutting himself off and reaching a careful hand out to touch Dean’s arm. He felt the angel’s soft hands on his skin and had to stop himself from shivering.

“Well,” he muttered, looking up from Cas’ hand on his arm, and up to his too-blue eyes. “You’re- wow.”

Cas laughed, and Dean already missed the sound. He watched as the angel’s hand left his arm. He felt a little cold. “I’ll be back. I-If that’s okay.”

Dean nodded quickly. “Yeah! I mean, you’re more than welcome to- next year?”

Nodding Cas gave Dean the smile that made his knees weak. “Next year. Talk to me. You know, the- I can’t reply but-” he stuttered through his words, but Dean shook his head, understanding what he meant. “I like your- your voice.” Dean had no response, but a nervous gulp and butterflies wreaking havoc in his stomach. “Okay. I’ll see you next year. I promise.”

“Next year.” He laughed quietly, his smile a little sad.

Cas smiled back, reaching out and putting his hand on the same spot on Dean’s arm. “See you soon, Dean.”

And with a _woosh_ , Dean blinked, and Cas was gone. He put a hand where Cas had touched him, and he laughed a little, biting his lip as he thought. Dean bowed his head and closed his eyes, a grin on his face.

_See you soon, angel._

**Notes for the Chapter:**

> Alright, maybe not as super slow of a burn for y'all, but for Dean and Cas, this is happening over YEARS. Poor babies ajskldjsld.
> 
> Alrighty, thank you sm for reading!! I love you (yes, YOU)!! Feel free to leave me a comment or check out my other destiel works while you wait for the next chapter ;) Thank you for starting this lil journey with me <3


	2. 2014 - Second Date?

**Notes for the Chapter:**

> I'M ENJOYING WRITING THIS IMMENSELY

**_Friday, October 31st, 2014_ **

**_6:22am_ **

Dean had spent the last year convincing himself that it wasn’t real.

Right after Castiel left, he locked up the shop and went home. Sam was barely awake when he arrived, only waiting to say goodnight before he went off to bed. Left alone in their living room, Dean had sat on the couch and thought. For a long while. At some point, he bowed his head, eyes closed.

_‘Hey, um, Cas. Castiel.’_

He immediately felt stupid, even though no one could see him (even if someone could, they wouldn’t be able to tell what he was doing). He let Cas know that, let him know that he was already second guessing what happened.

He also let him know that he really did hope Cas came back. Then, he told him goodnight.

After that, Dean's prayers were somewhat sparse. Sometimes, he’d tell Cas about a song he’d heard, or maybe he’d talk about Sam or the Impala. At some point, he told himself he was a major fucking idiot. He could literally only see the angel once a year. What kind of life was that? _Hi! I’m holding out for a celestial being that I can only see for, like, six fucking hours every Halloween!_ He felt like a nutjob.

But… he’d been able to _touch_ Cas. So something had to be _there_ , right? He was right to keep holding on, for 365 days. Things like that didn’t just happen, not in his world- there was always a reason.

Now, it was Halloween again. Though Dean had been hoping and waiting for this day, its arrival brought a queasy feeling, which didn’t leave him as he went about his tasks. He’d woken up and immediately realized what day it was.

Dean closed his eyes almost automatically. ‘ _Today,’_ he started off, his hands squeezed together. ‘ _I don’t- know what to say. Today’s Halloween. I started losing hope a little- I don’t know why, but I just- This is difficult. I’m used to seeing people I…_ care _about everyday. Or, at least, more than once a year.’_ He felt stupid, again, and almost ended it there. Almost. _‘I only talked to you for two hours and I can’t get over the fact that you were able to touch me. I could touch you.’_

With a nervous swallow, Dean finished his prayer. He had to get Sam up for school. _‘I miss you, angel. I like- I liked hearing your voice.’_

  
  


**_5:55pm_ **

Dean was on his couch in the living room. Sam was down the hall, working on homework. Dean had wanted to tell him about it, about Cas, but- he also didn’t want to look crazy if Cas decided not to show up. So he chose to tell Sam when Cas was there. If he was okay with it. He let Cas know where he would be earlier that day. Just in case.

He looked outside, at the setting sun, and furrowed his brow as it dipped lower and lower in the sky. Only a couple minutes until it was gone. Only a couple minutes until he’d figure out if he was crazy or not.

 _You’re definitely crazy,_ he thought to himself. _You’ve only talked to him for a couple hours. You’re pining after him over what? A touch and his hair?_

 _Fuck off. We shouldn’t have been able to touch,_ he justified to himself. _That’s some universe, destiny, connection shit._ He glanced out the window again, before looking back at his own hands. _And his hair is- it’s… cute._

The watch on his wrist read 5:58pm.

Dean squeezed his eyes shut as the sunlight faded from the room, so it was only illuminated by the ceiling lights. A soft _woosh_ sounded, and he waited, swallowing hard. His breath was uneven. His stomach was still turning.

“Dean.”

All his breath rushed out of him. His eyes didn’t open, but he felt a hand on his arm, and he almost crumbled.

“Cas.”

  
  


**_6:09pm_ **

“Sam,” Dean started, looking at his brother worriedly. He could see Sam’s wheels turning, his brain coming up with likely explanations for what he was seeing in front of him. The man with a trenchcoat and a faint silver halo who was standing in his living room next to his older brother. Dean could only imagine what was going through the kids head. “This is Castiel. Cas.”

As Dean expected, Sam caught on quickly. “So,” he started, peering at Cas through squinted eyes. “You’re the one who’s been driving my brother crazy for the past year?”

Cas’ laugh and Dean's embarrassed groan clashed in the air. “I- I guess so,” said Cas, glancing at Dean with a smile. “Cas. I’m an angel.”

Nodding, Sam smiled. “Sam. Human, obviously.” He then turned to Dean. “Okay, why are you being weird?”

Dean stared at his brother in confusion. “What?”

“You’re being weird. Over an angel. Like dad didn’t talk about them all the time. Like they don’t show up every year.” He nodded his head towards Cas. “No offence to you, but- What’s up with this one, Dean?”

Dean stuttered through a reply, unable to say anything that sounded right. So, he sighed, and took Sam's hand, placing it on Cas’ shoulder, where it promptly went straight through. Then, he ignored Sam’s face (if “duh” was an expression, it’s exactly what Sam looked like) and placed his own hand on the angel’s shoulder, where it landed firmly.

The wheels in Sam’s brain were turning once again, and Dean watched his thought process clear a day through his facial expressions “You…” Still confused, probably about to call Dean an idiot. “Wait. Oh.” A blink. Then, finally, with wide eyes and an open mouth: “ _Ohh!_ ”

With a breath, Dean’s hand fell. Cas caught it and let their fingers intertwine. Dean was pretty sure a piece of his soul just left for good- like a goddamn cartoon character. “Yeah,” he let out shakily. Cas squeezed his hand, probably to comfort him, but his voice only shook more. “Pretty cool, huh?”

Sam laughed, a shocked sound. “Yeah, way more than just- I mean, I get why you’re being weird now. Weirder than usual. There’s only so much this could mean, and it’s probably- _Woah_.”

“Okay, okay.” Dean let go of Cas’ hand to push Sam down the hallway. “Go away. I just wanted you to know, so you could help me figure out what it means. Now _you’re_ being weird.”

Practically running down the hall, Sam made his way to his room. “Yeah, no, you two- I mean, I’m gonna google some things and- I’ll be back after… this,” he shouted, before his bedroom door clicked shut.

Dean groaned loudly. He heard Cas laugh.

“Shut up, you,” he said, returning to Cas as he ran a hand through his hair. Dean watched Cas’ impossibly blue eyes, and his unfairly powerful smile.

The angel hesitantly opened his arms, and Dean collapsed into them. First hug. With an angel. His life was turning out to be so goddamn weird.

(Did a first hug count as a milestone? He wasn’t sure.)

“I like him. Your brother. Sam.” Dean listened as Cas spoke, those butterflies still not leaving him alone. “He’s smart.”

Dean laughed, the sound muffled against Cas’ shoulder. He took a deep breath. _Cotton? And… seabreeze and honey…_

“He’s the smartest person I know,” Dean replied, before he pulled away to look at Cas. “How come you aren’t super awkward? Why do you seem to fit with all our weird little human customs so easily? I honestly didn’t expect you to know what a hug is.”

Cas blinked. “I come here every year, Dean. For thousands of years. I pick up a couple things every now and then.”

“Oh.” Dean blinked back, then gave him a shy smile. “Right. Gotcha.”

Cas laughed, and even though Dean had _hours_ before the other had to leave, the sound still made him want to cry. “Angels are usually a bit… awkward, though, so you are right. There are some things you do which I will never fully grasp.” Dean didn’t respond, and when Cas looked at him, he was staring with his brows furrowed. He looked worried; like he didn’t believe this was anything, and he was afraid he couldn’t stop wasting his time. Cas gave him a small, understanding smile.

Dean sighed.

  
  


**_7:34pm_ **

Dean squeezed Cas’ hand, half affectionately, half making sure he was still there. “So, you heard me?”

They were lying on the ground in the living room, the small coffee table pushed to the side so the space between their TV and couch was empty. Dean thought the couch felt weird, and he didn’t want to take Cas to his fucking _bed_ , so the floor was the best option. Cas lay next to him, Dean's head turned to watch as Cas closed his eyes. He felt Cas’ hand reaching out, and he intertwined their fingers immediately.

“Yes.” He watched Cas’ mouth move, then looked back at his closed eyes. “My favorite thing that you told me- you said Sam got into… Stanford?” Dean made a noise in agreement. “I have no idea what that is. Not a clue. But you sounded so excited about it and so… proud. I couldn’t help but be a little proud, too, even if I’d never met Sam.”

Dean listened quietly, his chest full of warmth, and he decided that he could have kissed Cas right there, just for those words alone. Instead, he watched as Cas turned toward him and opened his eyes. The blue he was met with was deafening, the visual equivalent of an ocean roaring in his ears.

“Do you want to go for a drive?” Dean asked, eyes darting away from Cas’ stare. “I mean, I’m- I have some issues when it comes to… this.” He gestured between them with the hand that wasn’t in Cas’. “Driving always makes it easier for me to think. Or do anything, really.” He didn’t hear Cas reply, and he went on with his rambling. “Maybe I’m overthinking this? I mean, I’m talking about my fucking- my ‘commitment issues’ and this is the second time I’ve seen you- this doesn’t even count as a second date, does it? Goddamn, maybe I should shut up-”

“A drive sounds nice.” Dean looked up and was met with that painfully blue stare. He swallowed. Cas continued. “And I- if you’re okay with it, this could be- I mean I’m out of touch when it comes to, you know, humans and- and dating but…” He laughed a little. “You make me really, um, nervous. This could be a second date. If you want.”

With a soft laugh, Dean pushed himself up on one elbow, looking down at Cas. “Yeah, let’s go for a drive. I think it’d make a good second date. And… you make me nervous, too, angel.”

He could swear that Cas’ cheeks turned pink.

  
  


**_8:45pm_ **

They’d left Sam at home, Dean calling out that they were going out for a bit. Sam had raced out of his room, and Dean had told him to shut up before the kid had even said a word.

“You’re taking him to the park, right? I swear to God, Dean, this is obviously some sort of soulmate thing, and if you fuck this up for yourself-”

“Jesus, Sam, obviously.” Dean pulled his brother in for a quick hug, ruffling his hair (it was getting difficult. Sam was taller than him, now). “Go back to your nerdy research stuff, before you make me too nervous. We only have so long.”

Sam disappeared to his room. Dean walked out the front door, closing it behind him. He found Cas standing in front of the Impala, looking up at the stars. He turned when he heard Dean’s footsteps, and gave him a quick smile. Dean’s breath stuttered. “Are we ready to go?”

Dean nodded, opening the passenger door for Cas, who thanked him and got in. Cas continued. “I’ve never- I haven’t been in a car before. I usually just-” he snapped his fingers, “- get where I need to be.”

“Must be nice,” Dean laughed, before he closed Cas’ door and went around the car, getting into the driver's seat and starting the car. “But, driving is nice, too. Time to just think about things. Or nothing. Or just… listen to music.” He turned the volume up and the tape he’d left in there started playing. AC/DC’s ‘Back in Black’. 

Cas stared at the radio and then at Dean. “Music has changed a lot.”

Dean’s laugh was loud, and Cas watched with a small smile as some of the tension melted from the man's shoulders.

  
  


**_9:03pm_ **

“What do we do here?”

Cas was seated on the hood of the Impala, Dean next to him. Their hands were resting between them, their fingers barely touching as they looked out at the stars. The Impala was parked on a gravel path, looking out over a large field, which Dean had described as a park. There was a handful of people out and around the park, and Cas could see what looked like a playground far off to his right.

Dean looked at him, then back up. “We, uh, just… hang out. Look at the stars.” He shrugged. “Or talk to each other.”

Nodding, Cas glanced at him. “And what about on- with a second date. What do people do?”

“Still, um- still talk.” Dean pursed his lips, looking at the ground. He felt like a fucking school girl, his heart beating so hard, he thought it was going to fly out of his chest.It didn’t help that Cas’ stare was extremely intense. Was it Dean thinking too hard, or did the blue in his eyes literally fucking _move?_. “Sometimes they… kiss.” He glanced at Cas for confirmation that the angel knew what that was. The look he received was incredulous. “Hey,” Dean said defensively. “I don’t know what angels do! Hell, maybe kissing is against the law in heaven or something.”

The laugh Cas responded with made Dean smile. He felt a drunk off the sound. “I’ll have you know, I am fully aware of what a kiss is.” His smile grew, and Dean's heart stopped. “I’m a little dated, but I know quite a lot about the basics.” Cas seemed to debate whether or not he should continue. He leaned back on his hands, head tilted back to look at the stars. “Somethings don’t change.”

Deans brain told him once more to kiss Cas. He told it to shut the fuck up.

  
  


**_10:36pm_ **

At some point, Cas had convinced Dean to take an old blanket out of his car so they could sit out on the grass. Dean spread the blanket out, tugging the corners so it would lay flat, before they both lay down on it, the same way they were in the living room.

“I think I like this… the second date.”

Cas pushed himself up on one elbow as he spoke, fiddling with a blade of grass. Dean thought it was adorable. “Yeah?” He responded, smiling at Cas.

The angel wrapped the grass around his own finger, before grabbing a couple more pieces and weaving them together. Dean watched. “Yeah,” he replied, still weaving the grass. “Tell me something.”

Dean looked at Cas with raised brows. “Um, sure. What’s up?”

“You said, sometimes, people kiss on the second date.” Cas was still playing with the grass. He dropped it and looked up at Dean.

Not knowing what to say, Dean made a quiet noise and nodded.

“Okay.” Then Cas looked at Dean like he was gonna say something. Dean's answer was already on the tip of his tongue. He watched as Cas opened his mouth. Closed it. Took a breath. “Can I kiss you?”

Dean almost forgot he was supposed to respond. “Y-yeah. God, yes.”

Cas lifted Dean’s chin, coming close enough that Dean could feel the angels breath on his lips. Cas’ eyes darted up to Dean’s, before he tipped forward and gently pushed their lips together. Dean leaned up to kiss him harder, eyes shut tightly. When Cas leaned back, breaking the kiss, Dean let out an embarrassingly disappointed sound.

“Huh,” Cas murmured, making Dean open his eyes. He watched as Cas trailed his eyes over Dean’s face. Rubbed a thumb over Dean’s bottom lip. “I’m guessing I did that right?”

“Cas.” Dean cleared his throat, reaching up to grab Cas’ coat, pulling him back down. “Less talking.”

Dean kissed him hard. Cas cradled Dean's jaw with one hand, as Dean’s hands found themselves tangled in the angel's hair. He hovered over Dean, straddling him and leaning down, as his lips trailed from Deans and down his neck. Dean made a soft noise- and Cas stopped.

“If human customs have remained mostly the same,” Cas murmured, his lips barely brushing Deans jaw, “then I believe we cannot go any further until - at least - the third date?” He pushed himself up, watching Dean’s face as he processed.

Dean stared at Cas with his mouth open. Then he let out a groan of a laugh. “You fucking- Jesus, Cas, you’re-” He kept laughing, and Cas rolled over so he was next to Dean on the blanket again. He intertwined their hands. “That’s a whole year. Usually, the third date is within a _week_.”

Cas liked Dean's laugh. It made him feel full. Happy. “Even though,” he grinned, tracing circles onto the back of Dean’s hand. “I’d like to do this the way you would.”

“I would be doing a lot more right now,” Dean muttered. But he was smiling. And he bumped Cas gently. “But I’ll settle for- maybe just another kiss.”

And with a grin, Cas obliged.

  
  


**_11:39pm_ **

“Couldn’t you use some angel magic to keep yourself here?”

They were back in the Impala. Cas said he wanted to experience being driven again before he had to leave. “You know I can’t,” he sighed, watching Dean’s profile as the man kept his eyes squarely on the road. “If I could, I would have done that last time, if only to figure out what was going on.”

Dean sighed, clenching his jaw. “I know. I just-” Cas watched as Dean swallowed. Cleared his throat. Glanced over at Cas, then away quickly. “I- I wish I could- see you. More, I mean.”

Cas didn’t say anything for a bit. Then he watched as Dean’s house came into view. “Okay, well,” he started, as Dean parked the Impala outside (Cas had learned that he’d named it ‘Baby’. He still didn’t understand why, but he decided to go with it). “Well. I have- a little surprise for you.” He winced at his own word choice, then looked at Dean, who was looking at him with a soft smile. “I’ve been- hold on, just- okay, could you do the… praying?”

The weird look Dean gave him only made Cas laugh wearily. He complied, though.

 _‘Alright, angel.’_ Castiel tilted his head, failing to hide his smile as he listened to Dean. _‘You’re being weird. Did I make you uncomfortable? You know, we don’t have to do anything on the third date. We could go out to eat- you have to respond for that to happen, though.’_

A chuckle, and Cas closed his eyes, furrowing his brows like he was doing something particularly taxing. **‘Dinner sounds… nice.’** He could _feel_ Dean’s eyes snap open and stare at him. **‘Though, I’d still like to do the usual human thing with you, too.’**

Before Cas had even finished, Dean was already leaning over the center console of the car. By the time his eyes were open, Dean’s lips were on his, and he just closed them again. When Dean pulled back, Cas almost followed him. But Dean started talking. “You’re unbelievable.”

Cas huffed a laugh. “Yeah, well. I found that it was torture- hearing you and not being able to respond.” His eyes lingered on Dean’s lips. Then darted over his freckles. “Hopefully- hopefully, this will make the year go by a bit faster.” He looked up and his heart stuttered as he was met with a sea of green. “A-and, I can- I mean, we- um… you’re- making me nervous again.”

Dean’s answer was a quick kiss, before he rested their foreheads together. “Good,” he said, barely suppressing a smile. “I like making you nervous for a change.”

  
  


**_11:57pm_ **

The silence was the last thing Dean wanted to hear. He was with Cas, standing right outside his front door. “Three minutes,” he sighed gruffly, looking at the ground and clenching his jaw.

Cas put a hand on the side of Deans face, tilting his head up slightly. “You’ll be fine,” he murmured, eyes tracing Dean’s features. “I’ll talk to you so much, you’ll be sick of me before I even get back.”

Laughing, Dean relaxed slightly. “Yeah, well, I don’t think that could happen.” He shrugged as he continued. “I do know that I will be as annoying as possible. Just because you won’t stop teasing me.” He smirked, tongue in cheek. “Maybe I’ll start teasing back.”

The grin Dean was met with made him want to drag Cas inside the house and stop the teasing all together. “At the risk of sounding a little less...angelic,” said Cas, wiggling his eyebrows a little and making Dean give him a wary look. “I’m only looking forward to it.”

Dean’s shocked comeback was muffled as Cas pressed one last kiss to his lips. It was short and sweet, leaving Dean’s heart aching as he watched Cas step back, letting go of him reluctantly. “Okay.” A sad smile on his face, he raised a hand to wave at Cas, chuckling. “Okay, I’ll- bye, Cas.”

Cas smiled gently, heaving a sigh before he nodded. “Goodbye, Dean.”

He blinked, and Cas was gone.

**Notes for the Chapter:**

> this was... what 3000 words long???? incredible. i think i'm gonna sleep until the next update.
> 
> i hope y'all like where this is going! as you can probably tell, the next chapter will have sexual themes. i'm not sure yet if it will be outright smut or just implied (so you'll only read right before and right after). lemme know if you have a preference!!
> 
> alright, thank you sm for reading!! leave me a comment with your thoughts, and I hope to see you in the next chapter!! ily, have a wonderful week <3


	3. 2015 - I love you

**Notes for the Chapter:**

> PLEASE READ!!!!
> 
> hey guys! i can't write smut for shit SO! i won't describe anything in detail, just the two making out before they [REDACTED], and cuddling right after. I'll add stars (***) right before and right after those parts, so if you don't even want to read the make out session, you don't have to :)
> 
> alright, let's go!!!!

**Saturday, October 31st, 2015**

**_10:00am_ **

Dean woke up to the sound of the world carrying on around him. And a voice in his head.

 **‘If I remember well,’** said the voice in his head, ‘ **then you should be awake right now.’**

Dean groaned, shooting back a particularly sour response. All he heard back was a laugh, before a fond **‘I’ll see you soon, love.’** The smile Dean felt on his own face made him groan again, before he got up and headed to the kitchen.

A note was left on the fridge. _‘Out with some friends, I’ll be staying with them for the night. Have fun. Don’t screw this up! - Sam.’_

Sam had come home to visit from Stanford, and he’d spent the time helping Dean out at Bobby’s garage. Dean, however, would tell you Sam spent more time teasing him than helping him. It was partially true.

Dean sipped his coffee, smiling as the taste washed over his tongue. _‘I hope you know_ ,’ he started, finishing off his drink, _‘that I’m not letting you off easy just because I get to see you today. In fact, I’ll make it worse for you.’_

He could almost feel Cas stiffen and sigh. It brought a smile to his face. Dean had learned, over many nights, that his prayers didn’t need to be holy to get through to the angel. In fact, since he’d figured it out, he’d tortured Cas with thoughts and images that would send the angel short circuiting.

 **‘Dean,’** Castiel responded as Dean made his way back to his room. **‘You’re evil.’**

 _‘I am.’_ A laugh from Cas, and Dean involuntarily bit his lip.

**‘I hate you. So much.’**

After starting his shower, letting the water warm, Dean sat on his bed, eyes closed and his head tilted back. He sighed. _‘Lying isn’t very angelic, y’know. You love me.’_

**‘That I do.’**

That word had tripped Dean up a couple times. He still hadn’t said ‘I love you’ to Cas, though the angel had said it in mid-September. It had made Dean choke on his own spit, and everyone around him had given him a very weird look. Cas had told him he didn’t have to say it back. He understood that Dean needed a little more time.

( _It’s been two years,_ he’d scold himself. _That’s ridiculous. Don’t people say it after, like, a month?_ )

He wanted to say it, though. So bad. He’d literally practiced it when he didn’t have Cas tuned into his thoughts. He was pretty sure Sam had heard him repeating it in the mirror. But everytime Cas’ voice filled his mind, he went blank and lost all his courage.

The voice in his head - not Cas, but one that sounded something like his dad - called him a chicken. He agreed.

  
  


**_5:59pm_ **

The sun was setting. Dean had checked when it was predicted to be gone, and he knew he had only 2 minutes.

He hadn’t done much that day, besides clean a couple things up. His room was a little less messy, his clothes put away neatly and his bed made. He’d made himself go out on a drive, and Cas had tuned in for a little bit. Then, he’d gone off to do whatever angels did for work, and Dean drove himself home, imagining Cas was in the passenger seat and practicing “I love you”s the whole way.

He still didn’t feel ready. He desperately wanted to be.

Now, the sun was fading quickly. Dean didn’t close his eyes this time as he waited. He knew Cas would come. He had to.

And as the sky darkened and the clock reached 6:01pm, Dean heard a soft _woosh_. He was out of his seat and in Cas’ arms in seconds, kissing him like they hadn’t seen each other in- well, a year.

Dean expected Cas to laugh a little, maybe crack a lovingly teasing joke, but the angel seemed to be as adamant as he was about not letting go.“I missed you,” Cas murmured in between kisses. “Even though I could speak to you, I-”

“I know,” Dean responded. His hands were in Cas’ hair (God, his hair was something. Dean couldn’t get enough of it), and he pressed his forehead against Cas’. His heart was in his throat. “I missed you too, Cas, so much, you- I- I love you.”

And there it was. (Maybe all that practice helped.)

The expression on Cas’ face changed, like something broke inside of him. He kissed Dean again, and the man felt like he was about to melt in the angel’s arms. “Dean,” he whispered, his hands pulling Dean closer by his hips. Dean let out a groan, and Cas only kissed him harder. He whispered again, more urgently: “ _Dean._ ”

***And before a second passed, Dean was balancing kissing Cas and leading the angel to his bedroom. He clumsily worked the lock behind him, and Cas pressed him against the door, kisses moving from Dean’s lips, down his neck. Dean whimpered, head tilted back, eyes screwed shut. A noise of protest escaped him as he felt Cas pull away, but he opened his eyes. Cas was looking at him in what Dean could only recognize as awe. His face flushed, color blooming in his cheeks. He tried to speak, and it came out in a tiny squeak. Dean cleared his throat. “Cas.”

Cas seemed to swallow with difficulty. “Dean,” he breathed, pressing a kiss to the man’s jaw. “Are you- You’re sure?”

Dean huffed a laugh and kissed Cas again. “Please.” He licked his lips. Cleared his throat. Tried again. “ _Please._ ”

Cas kissed him again, and led him to the bed.***

**_7:24pm_ **

Cas’ arms were around Dean’s waist, hugging him from behind. Dean had all but fallen asleep when they’d finished, barely awake as he tried to recover (and he desperately needed to recover. Cas was, at the risk of making a pun, heavenly). He didn’t know whether Cas had cleaned up by hand or with some angel magic. He was, however, now wearing an old t-shirt and soft pajama bottoms. He turned to face Cas, and his breath caught in his throat.

The angel was wearing one of Deans’ band t-shirts, specifically a Led Zeppelin shirt. He had red flannel pajama pants on, also from Dean’s closet. But Dean was mostly focused on his hair. It was sticking up in all the wrong places, some of it falling into Cas’ face. In his head, Dean dubbed it Cas’ “Sex Hair” and decided it was his favorite look on him so far.

“Sorry,” said Cas, smiling sheepishly. “I just borrowed them. Didn’t think the coat and tie would be too comfortable."

Dean laughed, kissing Cas quickly. “No, it’s okay. You look cute in them.” He watched Cas blush and Dean sighed. “You and your sex hair are gonna make me come at you for round two.”

Cas only turned more pink, but he was grinning as Dean chuckled at him. “That doesn’t sound like too much of a bad thing,” he teased, leaning forward to kiss Dean gently.

Dean kissed back, then pulled away, a smile on his face. “Don’t encourage me, Angel.” He sat up, and laughed as Cas voiced his complaints. “Come on. I don’t have any dinner reservations, but we could watch a bad movie.”

**_8:35pm_ **

Dean sat on the couch, moving close to Castiel. The two were still wearing the pajamas, and everytime Cas’ hair got smoothed down, Dean kissed him back into looking like a mess. They’d found some candy and popcorn in the kitchen, and while Cas had explained he didn’t need to eat, he found that he liked the candy enough to finish off most of the bag.

“You really just can’t get a stomach ache from all this sugar? Or a cavity?”

“Nope.”

Dean had picked a hallmark movie for them to watch. He knew it would be a bad movie, but he wasn’t really planning on paying attention to it. He was basically on top of Cas, the angel’s arms around his waist as they cuddled on the couch. Cas kissed the top of Dean’s head every once in a while, making him grin like an idiot.

**_10:02pm_ **

The movie was, as predicted, terrible. Dean laughed all the way through, explaining parts to Cas and cringing at the acting. By the end, Dean was still laughing, and he turned to Cas to tell him something about the ridiculousness of these movies. But Cas was already looking at him. That expression was back on his face, the one Dean couldn’t pinpoint as anything other than awe. He turned a bright shade of red. “Stop that,” he chuckled, pushing Cas gently.

The angel caught his hand and pulled him in for a kiss, which Dean reciprocated. “Stop what?” Castiel murmured, so close he was just talking into Dean’s mouth

“Looking at me like that.” Dean kissed him again, then pulled back, groaning as Cas did exactly that. “You’re making me so nervous.”

Cas pressed his lips to each of Dean’s knuckles, then intertwined their fingers, squeezing his hand gently. “Good. I love making you nervous.” He grinned and Dean’s heart pounded. “You’re cute when you stutter.”

Dean glared at him halfheartedly. “Sh-shut up, Angel. You’re- this is so unfair.” He groaned and buried his face in Cas’ shoulder, turning red as Castiel’s laugh filled the room. “You’re the worst. The absolute worst.”

Cas hummed, the sound vibrating through Dean’s chest. “Be as that may,” Cas said, his hands rubbing circles into Dean’s back, combing gently through his hair. “You know you love me.”

The butterflies that took over Dean’s stomach left him breathless. He turned to kiss Cas’ cheek, pulling back and glaring at him. “Yeah. I do.”

**_11:21pm_ **

“I don’t want you to go.”

Cas felt his heart break as Dean spoke. They had moved from the living room, now laying in Dean’s bed with their foreheads touching, talking about whatever came to mind. “I don’t want to go,” Cas replied, watching Dean as he refused to look up from playing with the angel’s hands. “I’d give anything to stay here. With you.”

Dean sighed and looked up, smiling sadly at Cas. “I definitely wouldn’t let you.” His heart still lept in his throat at the intensity of Cas’ stare, but he no longer had to look away. “I have no idea what God is like as a dad, but I wouldn’t want you to get in trouble.”

Shaking his head, Cas pulled Dean closer. “I’m sneaky. They haven’t caught me talking to you all year.”

“That’s against the rules?”

“...Maybe.”

Dean smacked Cas’ arm, laughing. “Cas! Playing the role of a rebellious teenager.” He exclaimed, raising an eyebrow.

Grinning, Cas kissed Dean quickly. “I love you,” he said, for the thousandth time that night. “I would go against everything for you, if I knew how. Rebel against heaven.”

“Don’t get too hasty, Angel.” Dean pulled him back for a longer kiss, soft and sweet. “As sexy as you would be straight out of a fight, I don’t want you on God’s personal hit list. Sneaky telepathy will be enough for me to survive the year for now.”

**_11:55pm_ **

Outside of the house, Cas and Dean stood, looking at the stars in the sky. Cas had changed back into his usual attire, but Dean stayed in the pajamas. The moon shone down, and Cas watched the light dance in Dean’s hair. “If you’re counting my freckles,” Dean said, smiling a little before turning to look at Cas. “You’re gonna need a lot more time than the 4 minutes we have left.”

Cas laughed, and– did Dean even have to explain at this point? It made him feel like he could fly. “I’ll put that on my to do list for next year,” he responded, smiling gently as he pulled Dean closer.

“Before or after the super fancy dinner I’m gonna have for you?” Dean said, looping his fingers in the angel’s belt loops.

With a grin, Cas kissed the bridge of Dean’s nose. “After, of course,” he said, his expression mischievous. “I’ll need uninterrupted time to kiss every freckle I can see.”

That comment made Dean turn a bright shade of read, and Cas laughed. “You’re- you’re gonna be the death of me, Angel.”

Cas hummed. “I’d hope not. I’m starting to get pretty attached.”

A sigh, and a quick kiss on the cheek. “I love you. I already miss you,” Dean muttered. (Fuck. He sounded like a lovesick teenager.)

“I love you, too.” Cas kissed him, long and slow, before pulling back and resting his forehead against Dean’s. “And I miss you, so much. All the time.” He smiled sadly. **‘Talk to me.’**

Dean’s answering smile was just as sad. _‘Of course. I always do.’_

One more kiss– and Cas disappeared.

**Notes for the Chapter:**

> ehehehe thoughts? i liked this chapter. as you can tell, i figured out how it's going to end. 3 more updates and we're done!!
> 
> let me know what y'all think! next chapter, as promised, Dean is taking Cas out to eat. It will be cute and a little awkward. love you!! <3


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